Cytotoxic Diterpenoids from <i>Euphorbia helioscopia</i>

Lu, Zhenyu; Guan, Shu‐Hong; Li, Xing‐Nuo; Chen, Guangtong; Zhang, Jinqiang; Huang, Huilian; Li, Xuan; Guo, De‐An

doi:10.1021/np0706163

Cited by 53 publications

(40 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 2 (12.5 mg, t R 11.8 min) has been isolated from F9-6 (0.4 g) under the same conditions. (2S,3S,4R,5R,7S,8R,13R,15R)-5,9-Diacetoxy-3-benzoyloxy-7,14,15-trihydroxy-9-oxojatropha-6(17),11E-diene (1): grayish, amorphous powder (0.1 mg); [α]25 D −160 (c 0.10, MeOH); for 1 H and 13 C NMR spectroscopic data, see…”

mentioning

confidence: 99%

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

et al. 2015

View full text Add to dashboard Cite

Three new jatrophane esters (1-3) were isolated from Euphorbia amygdaloides ssp. semiperfoliata, including an unprecedented macrocyclic jatrophane ester bearing a hemiketal substructure, named jatrohemiketal (3). The chemical structures of compounds 1-3 and their relative configurations were determined by spectroscopic analysis. The absolute configuration of compound 3 was determined unambiguously through an original strategy combining NMR spectroscopy and molecular modeling. Conformational search calculations were performed for the four possible diastereomers 3a-3d differing in their C-6 and C-9 stereocenters, and the lowest energy conformer was used as input structure for geometry optimization. The prediction of NMR parameters ((1)H and (13)C chemical shifts and (1)H-(1)H coupling constants) by density functional theory (DFT) calculations allowed identifying the most plausible diastereomer. Finally, the stereostructure of 3 was solved by comparison of the structural features obtained by molecular modeling for 3a-3d with NMR-derived data (the values of dihedral angles deduced from the vicinal proton-proton coupling constants ((3)JHH) and interproton distances determined by ROESY). The methodology described herein provides an efficient way to solve or confirm structural elucidation of new macrocyclic diterpene esters, in particular when no crystal structure is available.

show abstract

mentioning

confidence: 99%

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Euphorbia helioscopia L. has been used to treat malaria, bacillary dysentery, osteomyelitis, and tumor in Chinese folk medicine (Hua et al, 1999;Gao, 1997). Up to now, only one obvious cytotoxic macrocyclic diterpenoid ester has been reported from this plant during the past three decades (Lu et al, 2008). Bioassay-guided phytochemical study on E. helioscopia revealed a new cytotoxic macrocyclic diterpenoid ester (1), together with seven known analogues (2-8).…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic macrocyclic diterpenoids from Euphorbia helioscopia

Tao

Hao

et al. 2008

Arch. Pharm. Res.

View full text Add to dashboard Cite

A new cytotoxic macrocyclic diterpenoid, euphornin L (1), together with seven known analogues were isolated from the plant Euphorbia helioscopia L. The structure of 1 was elucidated by spectral data and X-ray crystallographic analysis. Euphornin L (1) and euphoscopin F (2) exhibited significant cytotoxicity against HL-60 cell lines with IC(50) values of 2.7 and 9.0 microM, respectively. The 13C-NMR data of euphoscopin F (2), epieuphoscopin B (3), euphoscopin B (5), and euphoscopin C (6) were also reported for the first time.

show abstract

“…The IR spectrum suggested the presence of ester carbonyl (1743 cm −1 ), carbonyl (1715 cm −1 ), α , β -unsaturated keton (1675 cm −1 ) as well as a characteristic band for the aromatic ring (1602 and 1454 cm −1 ) functionalities. Based on those known jatrophane-skeleton diterpenoids with acyloxy groups from E. helioscopia 5, 9, 12–14 , 1 H and 13 C NMR resonances of 1 showed a set of typical signals for polyesterified jatrophane-type diterpene nature as well (Table 1). The 1 H NMR spectrum of 1 in CDCl 3 implied a benzoyl group [ δ H 8.05 (2 H, dd, J = 7.8, 1.2 Hz, H-2′ and H-6′), 7.60 (1 H, t, J = 7.8 Hz, H-4′), and 7.47 (2 H, t, J = 7.8 Hz, H-3′ and H-5′)], a pair of cis olefinic protons [ δ H 6.45 (1 H, dd, J = 10.2, 2.4 Hz, H-7), and 5.86 (1 H, d, J = 10.2 Hz, H-8)] and two oxygenated methine protons [ δ H 5.62 (1 H, d, J = 1.8 Hz, H-14), and 5.26 (1 H, dd, J = 7.2, 2.4 Hz, H-3)].…”

Section: Resultsmentioning

confidence: 99%

Heliosterpenoids A and B, two Novel Jatrophane-Derived Diterpenoids with a 5/6/4/6 Ring System from Euphorbia helioscopia

Mai

Liu

et al. 2017

Sci Rep

View full text Add to dashboard Cite

Heliosterpenoids A and B (1 and 2), two unprecedented jatrophane-derived diterpenoid esters with a novel 5/6/4/6-fused tetracyclic ring skeleton, were isolated from the whole plants of Euphorbia helioscopia. The structures of 1 and 2 were elucidated by extensive spectroscopic methods and electronic circular dichroism (ECD) analyses. The plausible biogenetic pathways of 1 and 2 were postulated. 1 and 2 were found to be potent inhibitors of P-glycoprotein (ABCB1) and 1 also exhibited cytotoxicity against MDA-MB-231 cell lines.

show abstract

Cytotoxic Diterpenoids from Euphorbia helioscopia

Cited by 53 publications

References 12 publications

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

Cytotoxic macrocyclic diterpenoids from Euphorbia helioscopia

Heliosterpenoids A and B, two Novel Jatrophane-Derived Diterpenoids with a 5/6/4/6 Ring System from Euphorbia helioscopia

Contact Info

Product

Resources

About